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Jamaica

$114+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
Sun 12/211:05 pmMBJ - ORD
1 stop12h 25mSpirit Airlines
Deal found 10/30$354
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Fri 12/191:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Deal found 10/30$355
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/28:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Fri 12/192:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 10/30$356
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Sun 11/231:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
Deal found 10/29$360
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/17:17 pmORD - MBJ
1 stop14h 00mAmerican Airlines
Fri 12/53:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 10/29$361
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:23 amORD - MBJ
1 stop10h 11mDelta
Thu 12/111:55 pmMBJ - ORD
2 stops23h 15mDelta
Deal found 10/29$362
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:00 amMDW - MBJ
1 stop7h 11mDelta
Wed 12/101:55 pmMBJ - MDW
2 stops20h 59mDelta
Deal found 10/29$362
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:00 amORD - MBJ
1 stop6h 02mMultiple Airlines
Sun 12/712:13 pmMBJ - ORD
1 stop25h 39mMultiple Airlines
Deal found 10/29$363
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/45:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Sun 11/91:07 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
Deal found 10/29$365
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/193:26 pmORD - MBJ
1 stop19h 36mSpirit Airlines
Thu 11/271:07 pmMBJ - ORD
1 stop8h 20mSpirit Airlines
Deal found 10/29$366
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Thu 12/183:45 pmMBJ - ORD
1 stop8h 30mAmerican Airlines
Deal found 10/30$367
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/143:20 pmORD - KIN
1 stop19h 54mMultiple Airlines
Wed 12/241:19 pmKIN - ORD
1 stop26h 43mMultiple Airlines
Deal found 10/28$368

Cheap flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$353
(Kiwi.com)

One-way from

$114
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$581

Good round-trip deal

$422 or less

Good one-way deal

$195 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Chicago (CHI) to Jamaica
Search Deals
One-way flight from Chicago (CHI) to Jamaica
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Jamaica.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Chicago

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/11

5:05 am-12:05 pm

1 stop6h 00m

Montego Bay Sangster Intl

Sun 1/25

1:12 pm-11:42 pm

1 stop11h 30m

$353

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 11/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 11/16

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/11

6:05 am-2:37 pm

1 stop7h 32m

Montego Bay Sangster Intl

Sun 1/25

2:48 pm-6:13 pm

Nonstop4h 25m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

6:05 am-2:37 pm

1 stop7h 32m

Montego Bay Sangster Intl

Wed 1/14

2:48 pm-6:13 pm

Nonstop4h 25m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

5:30 am-4:33 pm

1 stop10h 03m

Montego Bay Sangster Intl

Wed 12/10

1:55 pm-9:39 pm

1 stop8h 44m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/11

10:09 am-3:22 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Sun 1/25

3:12 pm-6:51 pm

Nonstop4h 39m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/1

5:23 am-4:34 pm

1 stop10h 11m

Montego Bay Sangster Intl

Thu 12/11

1:55 pm-12:10 pm

2 stops23h 15m

$362

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/2

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

Thu 12/11

2:29 pm-11:47 pm

1 stop10h 18m

$362

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/2

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

Tue 12/9

5:58 pm-9:54 am

1 stop16h 56m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, February is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $258). Flying from Chicago to Jamaica in March is currently the most expensive (average of $419). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Jamaica in the afternoon. If you’re flexible enough to do this you can expect to save up to 61% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Chicago to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated October 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Jamaica?

    A quick flight from Chicago to Jamaica can take about 4h 04m. Spirit Airlines provides one of the quickest options available for as low as $356. There are 1724 mi between Chicago and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $153 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $153 and American Airlines from $157 one-way.

  • What are the most popular routes from Chicago to Jamaica?

    The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $786 for a flight from Chicago to Jamaica. The cheapest flight overall is $157 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $289.

  • Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

    Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

  • Can I find deals for business class flights from Chicago to Jamaica?

    Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jamaica?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $258). Flying from Chicago to Jamaica in March is currently the most expensive (average of $419). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Providenciales flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
Midway to Montego Bay flights
Midway to Oranjestad flights
O'Hare Intl to St. George's flights
O'Hare Intl to Willemstad flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Castries flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Santo Domingo flights
St. Louis to Saint Thomas Island flights
St. Louis to Montego Bay flights
Midway to Providenciales flights
Midway to Simpson Bay flights
O'Hare Intl to St. John's flights
Midway to George Town flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Puerto Plata flights
St. Louis to Oranjestad flights
O'Hare Intl to Road Town flights
O'Hare Intl to Ponce flights
St. Louis to Simpson Bay flights
O'Hare Intl to Kingston flights
St. Louis to Nassau flights
St. Louis to Georgetown flights
St. Louis to Bridgetown flights
O'Hare Intl to Port of Spain flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to The Valley flights
Peoria to Luis Munoz Marin Intl flights
St. Louis to Willemstad flights
Midway to Santo Domingo flights
O'Hare Intl to Aguadilla flights
St. Louis to Castries flights
Midway to Castries flights
St. Louis to Santo Domingo flights

Top 6 airlines flying from Chicago to Jamaica

Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$186Average$709FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$245Average$449FlexibilityNo cancel feeOn-time65%
FrontierCheapest$333Average$662FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$375Average$627FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$433Average$656FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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